


Hollywood's Top Disciplinarian (Multiple Celebrities/You)

by gamerman1902



Series: RPF Spanking Stories [2]
Category: Actor RPF, Real Person Fiction, Singer RPF
Genre: Anal Beads, Anal Fingering, Anal Play, Anal Sex, BDSM, Bondage and Discipline, Breast Fucking, Butt Plugs, Choking, Corporal Punishment, Daddy Kink, Edgeplay, Explicit Sexual Content, F/M, Face-Fucking, Figging, Fisting, Gratuitous Smut, Nipple Play, Nipple Torture, Oral Sex, Orgasm Control, Orgasm Denial, Overstimulation, Rough Kissing, Rough Oral Sex, Rough Sex, Sex Toys, Sexual Roleplay, Sexy, Shameless Smut, Smut, Spanking, Tickling, Vaginal Fingering, Vaginal Sex, Vibrators, Wax Play, wedgies
Language: English
Status: In-Progress
Published: 2018-05-01
Updated: 2018-05-18
Packaged: 2019-04-30 11:42:11
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 10,078
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14496216
Author URL: https://archiveofourown.org/users/gamerman1902/pseuds/gamerman1902
Summary: When the female celebs of Hollywood act up they get sent to you for punishment. You are Hollywood's Top Disciplinarian and its up to you to keep the biggest divas in entertainment in check. Everyone you see in the tags will get a chapter eventually and more people will be added to the tags as I come up with them. Very very Explicit fic involving lots of spanking and various other sexual acts. This is real person fiction. Read all disclaimers and tags. Don't like, don't read.





	1. Fergie

**Author's Note:**

> Disclaimer: This work is complete fiction and is totally fantasy. I don't have anything to do with any celebrity in this book and this is purely for fantasy and entertainment. If you don't like real person fiction or explicit sexual content, go back now. You've been warned.  
> P.S Every time you see "Y/N" replace it with your name.

You rub your large, firm hands together in anticipation for who’s coming in to see you today. Pop star Fergie choose to “experiment” with the National Anthem at the NBA All Star Game and failed miserably. Naturally her management was none to pleased and her bitch attitude about the whole debacle did not help so they booked the famous MILF a session with you: Hollywood’s Top Disciplinarian. Every actress, musician or model who chooses to be a brat gets sent to you and you use the old, noble art of corporal punishment to take them down a notch.

Naturally, your the perfect man for the job. You are a towering presence at 6 foot 4 so most women are completely off the ground over your lap. Your arms are muscular and firm, without a trace of fat. You have a six pack and a body that makes you look like you were chiseled rather than born. This is all without mentioning your gigantic hands. Rough and firm from years of taking naughty women and girls over your knee and instilling some discipline into them. Today, Fergie will be facing your wrath.

That national anthem was just absolutely horrendous. You struggled not to burst into laughter watching it on YouTube. You had a tough demeanor to keep up after all. Right on time, Fergie knocks on your front door and you tell her to come in. You lead her into your living room. The woman is older now but no less stunning. She has great curves which are complemented by the tight black dress she choose to wear. This should be fun… for you that is.

“Hello Y/N, um I’m here for my… punishment.” she manages to stutter out while playing with her fingers and looking at the floor. You can’t help but smirk. You’ll never get over the effect you have on women, turning them from strong and independent into acting like a naughty little girl about to get punished by her daddy. In fact, you happen to have a massive daddy kink and incorporate it into your discipline to further embarrass whoever you come across.

“I’m sure you’ve heard from some of your friends how this works but I’m not Y/N to you. You are to address me as daddy. That clear little girl?” you explain.

She looks at you in absolute shock and horror and you have to hold back a chuckle. Why are all these pop divas so damn dramatic?

“But...but I’m 43 years old! You can’t treat me like this!” Fergie exclaims. You simply shake your head. Time to take this woman down a notch.

“Look lady, your national anthem was so bad Colin Kaepernick stood up and told you to stop disrespecting the flag. Now your management sent you to me to atone for this and to teach you not to fuck around with things that are fine as is. Now little girl you will obey or I’ll take it up with your management. That clear?” you threaten. That got her.

“Yes daddy. Crystal clear.” Fergie murmurs defeated. She makes eye contact with you finally and sighs. You stand up, take her hand and lead her to your punishment room. It’s soundproof and has a variety of implements as well as a spanking bench. Fortunately for Fergie a simple OTK should suffice in this situation. You grab a comfy leather chair and set it in the middle of the room. You sit down and without warning, pull Fergie over your lap. You grab her waist and adjust her over your knee so her feet are completely off the ground and her entire weight is on your lap. You raise your right knee slightly so her ass is further arched up and easier to access.

“Alright little girl. This is your punishment. Simple hand spanking, 20 with the hairbrush, 10 with daddy’s belt.” you explain while you rub the pop stars upturned bottom. This tight little ass is so damn sexy. Fergie is certainly in great shape. The pop star is wiggling and squirming over your knee letting out little whimpers as your torment her ass with your constant rubbing and teasing. You like to do this. Tease the woman a little before you get to the spanking, make them anticipate it and catch them off guard. It’s working judging from Fergie’s bucking and squealing as your rub and grope her tanned globes through her tight black dress. You give them a tight squeeze and jiggle them up and down in your hands, playing with them like dough.

“Daddy please. Punish me already!” Fergie practically begs in frustration as she keeps squirming in your lap from your torment. The pop diva is begging for punishment. You love the sound of that.

“You don’t give the orders around here little girl. Since you asked though…” you trail off as you slam your palm against her right cheek, hard. She jolts forward and squeals at the top of her lungs. You give her left cheek the same treatment, reveling in the way your palm bounces against her ass and her whimpers and squeals. You go at a slow steady pace focusing on power rather than speed. Your giant palms slams down on each cheek as you alternate between the two. You also try to keep her off guard. Sometimes giving her right cheek a few slaps in a row, other times her left and then going back to your normal pattern of alternating. She’s already panting and whimpering.

All of a sudden you pick up the pace and go rapid fire slamming your palm right in the center of her ass as fast as you can. That really gets her kicking and screaming as the high heels she was wearing go flying across the room due to her kicking. You know the fleshy center of her ass can take it though, so you go even faster, loving how her bottom bounces around and jiggles wildly. You decide it’s time to bear her. You have to see her bare ass take the thrashing.

“Daddy! Daddy noo! Please daddy. I’m sorry daddy. Please stop daddy! I can’t take it daddy!” are just some of the things she was crying while you were thrashing her over her thin black dress but decide to finally give her a rest and stop. You rub soothing circles on her bottom and gently squeeze her cheeks as you give her a breather. For a few moments the only sounds in the room is her panting and you giving her a few gentle love taps. Then, you go for the zipper on the back of her dress and unzip it. Her eyes widen as you pick her up in your arms and pull the dress off her like she’s a little girl.

“Daddy! No please daddy no! I’ve learned!” she pleads as you firmly hold her against you with your right arm while your left hand pulls the dress off her, exposing her racy black bra and panties. You pick her up in your arms and drape her back over your lap like she weighs nothing. She whimpers as you knead her reddened ass in your hands. Then you abruptly grab her lacy black panties and pull them deep into her exposed buttocks.

“Owwww daddy nooo!” she cries as you firmly grip her undies that are now splitting her ass and pussy in half and resume your spanking. You go back to your rapid fire thrashing quickly getting mesmerized by the ways Fergie’s ass cheeks bounce around wildly as your large flat palm slams against her ass, flattening her skin only for it to bounce back to it’s natural, bubble butt form. She’s wiggling and bucking wildly but you keep a firm hold of her by her undies and she’s only making her wedgie worse.

“Daddy my ass is getting split in half!” Fergie complains. She’s desperately struggling against you iron grip but the black fabric of her panties has completely disappeared. Quite frankly your getting tired of her struggling and you might just tie her up but then you get an idea. You slow your pace and target her sit spots with precise, thunderous smacks that have the pop star howling.

“You want this wedgie to stop?” you ask calmly as you deliver a particularly hard smack straight to Fergie’s right ass cheek that causes her to be lifted of your lap and slam back down.

“Owwwwww! Daddy please! Stop giving me a damn wed-OW!” Fergie cries as you cut her of with another high impact smack on her other cheek that leaves a dark red handprint.

“I want to hear you beg. Beg for me to strip you naked and spank you if you want this wedgie to stop.” you issue an ultimatum. You then deliberately deliver a barrage of lightning quick smacks that causes Fergie to jolt forward and cry out as her pert ass is flattened by your large palm before regaining its normal shape.

“Okay! Okay! Daddy please strip me naked and spank me bare please!” Fergie cries out as you punctuate her words with another hard smack straight to her fleshy center.

“What’s that little girl? I didn’t catch that.” you tease roughly groping her ass and pinching her burning cheeks.

“I said I want you to spank me naked daddy! Please daddy I need it so bad!” she cries. Good God this woman is a natural! You quickly lift her to her feet and roughly rip her panties off before undoing her bra. You admire the woman before you in all her naked glory. You quickly yank her back towards you and straddle her over one knee which leaves her asshole and pussy much more exposed. Her eyes widen in fear at her new position straddled over your knee.

“Naughty naughty. I knew you liked this!” you exclaim as you tease her pussy with your fingers. You feel her fliuds leaking onto your thigh and shit that’s hot. You tease her entrance with two fingers drawing letters against her labia. She’s a shaking mess right now and you flick her clit a few times for good measure. She’s letting out all sorts of whimpering noises and moans and her legs are shaking wildly. You enter her with two fingers and quickly add a third as you feel her instantly clamp down on them. She’s so fucking tight and she’s dripping. You curl your fingers up and she shoots up. Her legs are shaking wildly and she’s moaning your name.

“Ohh Y/N! More please!” she begs. You would indulge her because she took her spanking like such a good girl… except she called you Y/N instead of daddy. You stop curling against her G spot and pull your fingers out. She whimpers at the loss of contact as a pool of fluid leaks out of her pussy. You flick her clit and give it a light pinch making her groan.

“You called me Y/N. I’m daddy to you.” you say stoically as she desperately humps and grinds on your leg trying to relieve herself. She’s practically grinding her pussy against your sweatpants trying to get off and it’s really freaking hot when she’s all desperate like this. You let her get oh so close to orgasm before you yank her off your leg and she falls on her ass.

“Daddy please!” she practically begs. You roll your eyes and relent. You tell her go get the belt while you get up and walk to a chest where you keep your sex toys. You get a buttplug, vibrator and lube. You sit back on your chair and she’s there with the belt in her hands. You grab it from her and pull her back over your lap. You spread her legs so you can access her tight little butthole. She lets out a throaty moan as you pour the lube directly on her anus and slowly rub it in with your fingers. You can feel her leaking all over your lap as you keep massaging her anus. Your sweatpants are certainly ruined right now. Without further ado, you spread her cheeks, and slowly insert the big black buttplug into her ass. She groans as it fills her completely and splits her ass.  
“If your a good girl during your belting, you get the vibrator. We will skip the hairbrush because I think this will be enough for you to learn your lesson. Understood?” you ask.

“Yes daddy. Thank you daddy.” she quickly replies. You nod as you bring the belt down hard on her butt plugged ass. Her ass bounces about wildly as the leather belt mark sears itself into her ass. Delicious. You bring it down again and again making her count each strike and say “Thank You Daddy” after each one. You bring the belt back far and let the leather slam into the back of her thighs causing her to cry out and leaving her ass and upper thighs very red. Yet she took it like a good girl so you finally grant her release. You take the white vibrator and place it against her pussy as she groans in pleasure. With your free hand you take the butt plug and pump it in and out of her tight asshole as she finally loses all her inhibitions and makes an even bigger mess on your lap. Her legs are shaking wildly and you help her ride out her orgasm before you pick her up and place her on her shaky legs.

“We’re done here but that butt plug stays in until I say so, got it? Now go stand in the corner and I better not see you move unless you want another spanking.” you warn. She quickly nods muttering a quick “Yes Daddy” and goes to stand in the corner, her butt plugged red ass on full display. You just sit back and admire your work. You love your job.

**Notes for the Chapter:**

> So that's the first chapter. Let me know what you think.


	2. Nicki Minaj

**Notes for the Chapter:**

> Disclaimer: This is pure fantasy and is purely for entertainment. I don't own anything to do with any celebrity.

You had gotten a call from an executive at Cash Money Records. Apparently, Nicki Minaj was out of control and they had not idea what to do. She was being a total diva, slacking off in the recording booth, blowing all her money and disrespecting various employees of the label. So naturally, it’s time for you to work your magic. You put on a pair of joggers and wait for Nicki to show up.

A few hours later, you hear your doorbell ring. You answer the door to see the rapper in all her glory wearing a pair of skinny jeans to show off her ass beautifully and a pink crop top that is far too small to contain her large breasts. She quickly blows past you before you even get to greet her and she is in for it now.

“Yo so what the the hell we doin’. Why my label send me to see some random buff dude in his big ass house.” Nicki rudely asked, not looking up from her iPhone. You narrow your eyes at her. She is gonna get it.

“You mean they didn’t tell you who I am? I’m the disciplinarian that keeps brats like you in line and you are due for a punishment little girl.” you explain. Her eyes shoot up at that. Apparently this is all news to her.

“Who the fuck do you think you are calling me a little girl you punk bitch?! You ain’t shit and what the fuck you mean punishment! I ain’t doing shit with you, you damn weirdo!” she spits. So you have to do this the hard way. Long story short, you throw the short woman over your shoulder and carry her into your punishment room kicking and screaming. Once there, you pin her to your spanking bench as you get out your handcuffs and cuff her arms together. Next you grab a ball gag and roughly shove it into her mouth before you fasten it around her head. Then, you grab a blindfold and fasten it over her eyes. Once she’s incapacitated, you roughly unbuckle her jeans and struggle to get them off over her huge ass. You finally manage to drag them off her legs and throw them on the floor. You can’t help but drool over the huge ass and thick thighs that are all yours to punish, now only covered by a skimpy pink thong wedged deep between her brown ass cheeks.

“Fuck I’m going to tear this ass up.” you say devilishly. She just screams and screams some more but with her ball gag you can’t make out a word she’s trying to say. So you just take her in your arms and place her in an underarm carry. She’s quite short and you’ve always wanted to dominate a woman with this position. You wrap your right arm securely around her waist as she helplessly dangles of the floor kicking and muffling out curses through her gag. You simply walk up to your wall of implements with poor Nicki struggling in your grip like she’s a small child. God, you love it when a fully grown woman is just as helpless as a little girl. Your getting a serious power rush from this. You finally decide on a decent sized brown wooden paddle.

“You really should’ve played nice little girl.” you say as you slam the paddle against her fleshy behind causing her to jolt forward in your grip. The room soon fills with the sound of wood making contact with flesh. She squirms and struggles under your arm as you are mesmerized at the sight of her two globes of flesh jiggling and quaking as you slam the paddle against them at a steady, meticulous pace. You slam the paddle down as hard as you can because you love the aftershocks that see her ass quivering so much even her thick thighs start to jiggle. All Nicki can do is whimper and groan through her ball gag as drool drips out of her mouth. Her brown ass is getting quite red as you give her jiggling ass yet another smack that causes her cheeks to bounce up and down in a mesmerizing fashion. 

“Fuck this ass is so damn hypnotic.” you groan as you deliver a strike to her thick thighs causing her thighs to jiggle and her legs to quiver as she twists and turns in the carry. You adjust her so her ass is up in the air while her upper body is pointing down toward the floor. The short woman is completely helpless dangling off the floor under your strong arm. You start smacking her ass with the paddle again making it jiggle up and down in a satisfying motion. After about 10 more swats where Nicki desperately wriggles and shakes her ass every which way trying to avoid the paddle’s wrath, you stop. Ironically her shaking her ass while the paddle slammed into it caused comical amounts of jiggling and bouncing. You couldn’t help but drool at the sight. With Nicki still under your arm, you grab your chair and pull her thong down before draping her over your lap. Time to really cop a feel of this juicy brown ass.

“Damn baby girl, I’m gonna have a ton of fun smacking this ass.” you say licking your lips. She groans through her gag in response. You grab both of her ass cheeks and give them a rough squeeze. You knead the juicy mounds of flesh in your hands while delivering some rough slaps to her ass in between all the rubbing, just to catch her off guard. You pinch each of her red ass cheeks causing her to kick her legs and squeal. You slightly spread her legs as you massage her inner thighs and run your hand up and down her legs. She moans and whimpers as you roughly grab her ass cheeks again and squeeze them tightly in your giant hands. The rapper is caught further off guard as you deliver a scintillating barrage of smacks to her famous backside causing it to jiggle like jello as she jolts further over your lap.

“Fuck, this ass was made to be smacked. The work you had done really came out well!” you tease as she curses through her gag. You keep delivering barrages of smacks to her ass as she kicks her legs wildly over your knee, but it does little to stop you from hitting your target. You roughly grab her throat and bend her backwards as you deliver brutal slaps to her jiggling mounds of flesh. Her breathing quickly becomes panting as she pleads through her gag as you engage in some breathplay, choking her before easing your grip when it becomes too much. You bend her as far back as she’ll go as you roughly smack her ass and start choking her again. You ease your grip when you think she’s about to pass out. You finally release her neck as her upper body falls back over your left leg.

“I would’ve been a lot gentler with you if you had some manners little girl.” you say as you spread her legs and tease her anus. You circle your finger around her tight little hole. Her ass cheeks are bright red at this point. You dip your pointer finger into her ass hole in an attempt to loosen it up. You insert your middle finger into her anus causing her to whimper as you stretch her anus using your fingers. Using your free hand, you grab her neck again and bend her backward in your lap to get a good look at her face as you roughly spread her anus with your fingers. She’s drooling all over herself and tears have rolled down her face. You release her neck as you undo her gag so she can speak. She pants heavily and gasps for breath as the gag hits the ground.

“Please please enough! I’ll listen alright? Just ahhh.” she doesn’t get to finish as you push your fingers further into her anus as your roughly pump her ass. You roughly rip off her top and undo her bra as you give her tits a squeeze. You gather her in your arms as you throw her over your shoulder to get some things.

“First off, you are to call me daddy. Second you will submit to everything I want from now on? Clear?” you ask.

“Yes daddy. Anything.” she easily replies. You crack a smirk. She’s coming around but your not done as yet. You really love the view of her big fat ass right next to your face like this. So you grab some lube, a massive purple dildo, some peeled ginger root and nipple clamps. With all this you go back to your chair and place her back over your lap.

“Daddy please. No more daddy.” she begs. Oh you love it very much when they beg like the submissive little sluts they are. In response you place all the items you gathered on her back as you roughly grab both her tits and knead them in your hands. The knockers on this one are just as impressive as her fat ass. You pinch her nipples and twist them in your grip causing her to moan and squeal.

“Oh shit daddy! Please, be gentler. Daddy!” she pants as you keep twisting and turning her nipples as she struggles fruitlessly over your lap.

“If any of the items fall on your back fall due to your struggling, I will cane your ass black and blue.” you warn as you give her nipples a particularly rough twist. She just whimpers in response, not liking the idea of her already bright red ass getting the cane. You finally stop mangling her breasts and torturing her nipples to get the metal nipple clamps from her back. You take each tit in your hand as you fasten the clamps around each nipple as she groans in response. You then go back to spanking her ass.

“Daddy no please!” she cries as you smack her ass at a slow place alternating between each cheek. You love the way her titties bounce up and down as her entire body jolts with the force of your smacks. Her ass and titties bouncing around like there’s not tomorrow is another reason you can’t help but smack this ass as much as you can.

“Daddy please! Stop daddy, I’ll do anything you want! Daddy!” she begs. Huh. The best part is you didn’t even have to ask her to. So you stop smacking her ass and instead get the bottle of lube and spread her cheeks. You pour it right onto her anus and watch it drip down to her pussy. She hisses as the cold lube makes contact with her hot skin. You grab her cheeks and mangle and mash them together. You spread her cheeks open and grab the dildo as you slowly insert it into her vagina.. She moans as the thick 9 inch dildo slides deeper and deeper into her until it fills her completely. Her walls quickly clamp down on the toy as vaginal juices begin leaking out of her pussy and run down her thighs. What a delicious sight. You finally grab the peeled ginger root and prep her anus for the figging by spreading her tight little asshole as far as possible with your fingers while you slowly slide the ginger root in her ass. You watch as you stop spreading her cheeks and her big ass quickly envelops both the dildo and the ginger root.

“Daddy it burns!” she screeches as the ginger root begins to have the desired effect as it releases its juices inside her anus. Her legs begin twitching and she suddenly becomes very jumpy as she wriggles over your lap.

“Easy baby girl. Don’t clench or it’ll burn worse.” you warn as you massage her burning ass. Nicki is now experiencing internal and external burning and judging from her shaking legs and twitching body, it’s doing its job. You pick her up in your arms and throw her over your shoulder as you walk over to a corner of your punishment room that you haven’t tried yet. That’s because it houses your brand new spanking machine. You uncuff her and strap her down over the bench, ass high in the air and legs spread to show off her plugged holes. Juices are running down her leg as her vaginal walls continue to clench down on the massive dildo as her anus is stuffed with a big piece of ginger root. What an amazing sight. Though you are more interested in her pretty mouth. The machine has a leather paddle that is automated and can be controlled with a remote.

“Listen here little girl. Your gonna give me a nice blowjob while you get a few licks from this machine. How long your strapped down depends on how good you do sucking me off. Got it?” you ask.

“Yes daddy.” she takes a deep breath. You start the machine and walk around so your right in her face. The machine slams the leather paddle into her sore ass which serves to push the dildo and ginger root further into her. You drop your pants and finally free your fully erect, nine inch cock. You shove it into Nicki’s mouth as you feel a warm pressure engulf your length and you look down at the rapper as she bobs up and down stroking the base of your shaft. The machine smacks her ass again causing her to let out a throaty moan against your cock. You grab her hair and force her down further causing her to let out a sexy little squeak just as the machine hits her ass again.

“Oh fuck yes! Take it just like that! Good girl.” you praise as you roughly force her down further so that your tip is prodding the back of her throat. You use both your hands to grab her hair and roughly start face fucking her, forcing her to rapidly bob up and down shoving you full nine inches down her throat. You then realize the woman has no gag reflex. This must be heaven. You feel precum leaking out of your tip, coating her throat. You pull out of her mouth to brush your head against her lips, coating them with your precum. With that you roughly shove your cock back in her mouth forcing her to deepthroat it as you roughly bob her head up and down your length causing drool and precum to leak from her mouth.

“Shit you take this like such a good little slut!” you praise. The rapper deserves credit. She’s giving you the best oral of your life while getting an ass beating. All the whimpering and moaning she does vibrates against your cock and she sounds so hot making the squeaking noises. Not to mention those delicious choking and slurping sounds as you forcefully bob her head up and down your cock to the point where her lips are touching the base of your dick. Shit, this is too hot. Your gonna become undone.

“Shit! I’m cumming!” you grunt as you blow your load inside her mouth. You slowly pull your dick out of her mouth to see it coated with your cum. Some of it has leaked out and is all over her face. She looks so fucking hot, you white sticky cum all over her lips, coating the inside of her mouth, her tongue and of course her throat.

“Good girls swallow.” you say as you turn off the machine. She does swallow every last drop and uses her tongue to clean the area surrounding her mouth. You pull your pants back up and walk around behind her again and the sight makes your hard instantly. Her ass cheeks are raw red, the ginger root deep in her anus and the dildo almost completely inside of her with juices leaking down her legs and forming a puddle on the floor. You are gonna take this ass. You slowly pull the ginger root out to relieve her of the burning sensation, but it also makes people horny.

“Hey baby girl. Daddy wants to take your ass tonight. Can I do that?” you ask as you walk up next to her and roughly grip her ass cheeks and rub your bulge against her ass.

“Shit daddy. I-I could use you back there.” Nicki admits.

“What do naughty little girls say when they want something from daddy.” you tease.

“Please daddy.” she easily replies. You pull down your pants again and free your dick once more. You slowly pull the dildo out of her vagina and replace it with three fingers that go knuckle deep. You start curling them inside of her against her spongy g spot.

“Uh ohhhhh. Daddy I want you in my ass so bad.” she moans.

“Gonna need more than that baby girl.” you torment her some more as you keep curling inside of her.

“Please daddy. I want you to fuck me until I can’t walk straight. I want you balls deep inside my ass! I need you to tear my asshole apart daddy!” she begs. You don’t need any further invitations as you pour lube on your cock and stroke it before plunging your head into her ass. She squeals as her ass envelops you cock, inch by inch. You keep pumping your fingers inside her pussy as you push further into her ass. Fuck she’s so damn tight. You look down to see her massive ass cheeks greedily gobbling up your cock and you almost lose it right there. Luckily you are better than that and keep pushing so you're balls deep inside of her and then you begin pounding her ass the best you can.

The room quickly fills with the sounds of your moans and cries as you roughly thrust in and out of her ass rapidly expanding her anus. Nicki screames at the sensation of getting rammed in both holes.

“Yeah my dirty little slut likes that huh? Here, you feel this?” you ask using your free hand to smear the cum that was spilling out of Nicki onto her thick thighs and ass cheeks. Fuck they look ever hotter glistening in her own arousal like that. You ram your cock in and out of her ass like clockwork until you feel your balls tighten. Your cock head keeps crashing against the wall of Nicki’s anus as you feel yourself on the verge.

“Fuck, your such a dirty little girl!” you scream as she lets out a high pitched cry and has the biggest orgasm of her life. (Probably.) She squirts all over you like a freaking water sprinkler but you're too busy ramming her from behind to care about her liquids all over your upper body right now. You cum shortly after, blowing an even bigger load than before and filling her ass with your creamy cum. You remove your dick to see that her anus has become a gaping hole that’s filled to the brim with your cum. Her legs are twitching, her body is shaking, she’s a whimpering mess and your cum is leaking out of her asshole and running down her legs.

“God damn daddy. I might have to be a bitch more often.” she half jokes.

“Still not enough for you little girl?” you tease. You can’t help but admire her in this state. Dominated, degraded and fucked like a little slut. Just the way you like it. Another job well done.

**Notes for the Chapter:**

> I really like how this chapter came out. Rihanna is probably next.


	3. Rihanna

You might be a disciplinarian but some women actually enjoy your company. There are some stars who schedule sessions with you of their own free will. They like to be spanked, dominated and fucked by you. One of them is Rihanna, who texted you this morning that she wants to see you. You were all too happy to oblige.

Rihanna: Hey Y/N, I’ve been a very bad girl lately. I might just need some correction.

Y/N: Is that so? Do you need to see daddy baby girl?

Rihanna: I think so. Maybe you can teach me some manners.

Y/N: A naughty girl like you could certainly use some.

Rihanna: What are you gonna do about it Y/N?

Y/N: Drop by in a few hours and find out.

Rihanna: Ok daddy.

You kill some time for a few hours waiting for her to show up. She finally arrives in the afternoon and you open the door for her. She’s wearing a white tank top and some black booty shorts. A simple outfit but it still looks stunning on a beautiful woman like her. You quickly usher her inside your house and you greet each other before going to your vaunted punishment room.

“So you’ve been a bad girl eh?” you ask as you grab your favorite chair and drag it to the center of the room. You sit down and look at the woman in front of you who is biting down on her lip and twirling her hair. Damn she pulls off the whole “naughty girl” act far too well.

“Yes daddy, I’ve been really naughty lately.” she shyly responds. Rihanna is usually seen as a fierce and independent woman but you love the effect that you have on her. You much prefer her as the shy and flustered girl standing in front of you.

“Well then I think you’re due for a punishment. Go ahead and pick out three implements for me baby girl.” you order. She nods and walks up to your wall of implements and looks it over. She grabs a small leather studded paddle, a wooden spoon and a riding crop as she shuffles back over to you and places the items at your feet. She certainly doesn’t want you to go easy on her if she picked out those implements. Not that she ever wants a soft spanking. She’s a masochist which is why she’s one of your favorite people to play with.

“I think you know the drill by now yeah?” you imply causing her to nod and take of her tank top and undo her racy black bra. She then pulls down her tight black booty shorts revealing her black thong wedged in between her generous glutes. You beckon her over and pull her over your lap. You roughly grab her breasts and give them a tight squeeze as you massage her ass with your other hand.

Rihanna groans as you pull her thong further up her ass and it gets wedged in between her thick pussy lips. You move your fingers as you play with her newly exposed pussy and she shudders as you slowly run your finger over her entrance that only has a soaking wet piece of thin black fabric that is keeping you from full access. You stop teasing her pussy and deliver a barrage of rough smacks all over her ass that cause her to shake and moan. She wraps her arms around your leg to steady herself and buries her head into your leg as she takes your rough spanking like the good girl she is. She whimpers as your rough smacks land right in the center of her fleshy ass causing her cheeks to jiggle wildly. You pull her further over her lap as you start alternating between each cheek delivering rapid fire smacks. You stop the hand spanking to observe her reddened bottom.

“Now it’s time for the real spanking to start.” you say as she just bites her lip and nods. You pull her soaking wet thong out of her ass cheeks and off her long legs and grab the wooden spoon. You place the implement on her back as you take a moment to knead her lovely mounds of flesh and admire her naked, curvaceous body shuddering and twisting over your lap. You torment her by slowly inserting two fingers into her pussy and pumping her until she’s squirming and squealing over your knee. She groans as you abruptly pull your fingers out and deliver another smack to her ass. You spread her cheeks once again and trace her pussy with your finger causing her legs to shudder uncontrollably.

“Daddy please… I-I need some relief!” she begs. You respond by spreading her bubble butt and slowly dragging your tongue along her soaking wet pussy. She cries out and wraps her arms tighter around your legs as you tease her with your tongue. You prod her now swollen pussy lips with your tongue as you tease her enough to keep her right on the edge. Right where you want her.

“Daddy I can’t! This is torture!” she whines. You respond by spitting on her anus and lubricating the tight little hole with your saliva before shoving two fingers in and stretching it out.

“Fuck! Ohh my God! Da-Daddy…” she trails off as she forgets how to speak as you push your fingers as far as they’ll go deep into her tight little butthole. You grab the wooden spoon and deliver ten hard strikes to her right cheek causing it to bounce up and down. You feel her butt clenching around your fingers as you roughly prod further into her.

“Clenching makes it worse baby girl.” you warn as you give her left ass cheek the same treatment. She follow your advice and unclenches as you slowly remove your fingers from her anus. You feel your knee soaked and again prod her pussy as she jerks up at the sudden intrusion. Even the smallest of grazes against her pussy makes her squeal and shudder in your lap.  
“I’m going to thrash this ass so hard.” you warn as she just whimpers in response. You adjust the pop star over your knee so her legs are spread and her pussy is in direct contact with the fabric of your pants. She is clearly over stimulated right now and you plan to take full advantage. You take the wooden spoon and thrash her ass about as hard as you can, landing smack after smack on both of her now wildly jiggling globes of flesh. This is a brutal spanking but you know her ass is thick enough to take the beating and deep down she likes the pain. She cries and twists over your lap which causes friction between your knee and her pussy. You somehow pick up the pace even more and land a series of rapid fire smacks with the spoon, causing Rihanna’s creamy brown ass to turn an angry red color. All through the beating she is inadvertently grinding all over your knee and you can feel her pussy leaking.

“Daddy please!” she cries through her simultaneous crying and moaning. You know you’re causing her immense pain and pleasure at the same time. She can thank you later.

“I’m not stopping this beating until you cum little girl. Cum for daddy. I feel how wet you are.” you order. Her legs shudder as you target her thick thighs causing her flesh to jiggle and her to pull herself further into your lap. She gyrates her hips as her pussy rides against your thigh. You can feel her juices soaking through your pants and your getting rock hard. Rihanna is grinding against your knee so desperately it looks like she’s twerking as her ass is getting brutally assaulted with the wooden spoon. She’s desperately trying to get her feet back on the ground so she can get better leverage but she’s helplessly dangling over your lap with your knee in between her legs. You even raise your knee further just to torment her more.

“Fuck fuck fuck!” she screams as she keeps humping your knee to the point where her hips and core are slamming against your hard dick. You groan loudly as she’s practically humping your crotch at this point and her pussy is soaking. She lets out a loud cry as you slam the spoon into the middle of her fleshy ass. She jolts up and wraps her arms around your neck, burying her face in your shoulder. She adjusts her position so she’s straddling your lap and goes to town grinding all over you as you keep on smacking her ass like there’s no tomorrow. She’s pretty much humping your clothed cock and you feel like you might cum in your pants if this keeps up. She screams as she finally achieves orgasm and collapses into you as she shudders through the aftershocks. You drop the spoon and wrap your arms around her and cradle her into your chest.

“That was a pretty smart strategy adjusting your position on my lap like that. Unfortunately, I’m going to have to punish you some more for not staying in position.” you tell her. The pop star groans and cuddles further into your chest cooing and pleading with you to let her off easy. She looks at you with a adorable little pout and big hazel puppy dog eyes that are gleaming with unshed tears. You cradle the Barbadian superstar in your lap and kiss her.  
“Please, please, please Daddy! No paddle?” she cooes as you kiss her some more and swallow her moans. You capture her bottom lip and roughly bite down on it causing her to whimper. You attack her lips with your tongue, asking for access which she gives. You two then get locked in a heated kissing session as you rock the pop star in your lap. Your tongues clash and dance in each others mouths as you swallow each others moans and graze teeth. She stops kissing you and shoots those hazel puppy eyes at you again. You tease her pussy with your fingers again and she cries out your name at the initial shock and then mutters profanities under her breath as you play with her overstimulated pussy.

“Now baby girl, you know how this works. You can beg and coo and pout all you want but your getting those other two implements.” you affirm as you abruptly stick two fingers in and her pussy clenches around them. She grabs ahold of you and buries her face in you chest as she lets out the sexiest moans and cries you’ve ever heard.

“Actually I’ll let you have a choice. You can either take the rest of the spanking and I’ll relieve you right now or you can choose not to take the spanking and go home unsatisfied. You want more or not?” you offer. She looks up at you and practically sobs out a “yes” as she begs for relief. That’s a good girl. You take her in your arms and over to the bed you have in where you lay her down on her back and kneel in front of her soaking wet center. She quickly wraps her legs around your face and your roughly grip her juicy thighs. The pop star looks down at you with a lust filled gaze and her eyes have gone from puppy dog to smoldering. You lick and nip at her sensitive center as she tangles a hand in your hair. You slide your tongue down and probe her entrance, earning more than a moan.

“Daddy, I-I need more.” she whines while you hum against her center. She’s practically sobbing at this point and you smirk before sliding your tongue into her warmth completely, eliciting all types of noises. You slowly move your tongue inside of her, reaching every spot that can drive her crazy as you eagerly lap up her juices. The pop star just writhes and shudders as she struggles to stay still. She’s still so sensitive from her previous orgasm that this will have a heavy effect on her.

“Daddy, I need you here.” she begs as she guides you to her clit. You listen to her easily and wrap your lips around the bundle of nerves and snake your tongue out to run over her clit. You hold eye contact with her before you add more pressure with your tongue which causes her to squeeze her eyes shut and let out quite the high note. Maybe she’ll write a song about you. You probe at her entrance with two fingers as you lap at her center. There’s no problem with making her cum over and over, but with that comes the overbearing stimulation that you love to torture her with. You slowly insert two fingers and thrust slowly as you keep on eating her out.

“Ohhh fuck yes Daddy! Just like that!” she moans in approval. You grin and curl your fingers upward to hit her rough G spot as she lets out an unrestrained moan. You continue to thrust faster as you keep curling your fingers and sucking her clit. You suck at her center and quicken your pace to her whines and moans. She cries out in pleasure as you gently nip at her clit and send her over the edge completely and you seperate your mouth from her clit to spread the new wetness with your coated fingers. You go back in to lazily lap at her center before circling her clit with added pressure once again, earning a sharp cry and some delicious whimpering sounds.

“I-I can't. Daddy th-this is too much.” she sobs in pleasure, her hips lifting off the bed only for you to roughly shove them back down.

“One more baby girl.” you say and she just heaves on the bed, completely spent. You pull her towards you and lift her legs over your shoulders and place kisses all over her smooth inner thighs. You lap up the copious amounts of wetness coating her, driven by her moans and little squeals and whimpers of approval.

“Daddy please. Y-Your tongue.” she sobs. You pick her up in your arms before laying down on the bed and lowering her down over your mouth so she could ride your face. She starts lifting her hips and lowering them slowly as she grinds her core on your mouth. You roughly palm her sore ass and nip her clit as she controls the pace. You curl your tongue upward to reach her spongy patch as you move your hands to rub her clit. You thrust your tongue harder inside of her as she struggles to steady herself. You let out a growl against her clit and the vibrations really affect her.

“Daddy yo-you can't… Oh fuck!” she pants as you grab her hips and force her to grind on your face faster. She’s so fucking hot when she’s panting. You skillfully move her tongue to lap at her juices as you enter two fingers inside of her unexpectedly causing her to squirm. She rests her face against the headboard, her face scrunched up and cheeks rosy as an explosive orgasm comes over her. You gently bite at her clit and curl your fingers to hit the rough patch to send her over the edge. She keeps squirming and writhing above you as you lazily lap up her juices and she squirts all over your face before collapsing beside you and curling up in a ball, the aftershocks still hitting her. You touch your face to find her fluids all over it and you can’t help but chuckle.

“So-Sorry daddy. I-I didn’t mean to-” she starts before you cut her off by putting your fingers in her mouth and making her taste herself.

“Don’t apologize for that baby girl. Maybe I can make you squirt again sometime. That was really fucking hot.” you whisper as she just moans and sucks on your fingers. You take off your now ruined clothes and strip completely naked before walking over to get the studded paddle and riding crop as you sit on the edge of the bed. You beckon her over and she obediently lays over your lap and rubs up against your now bare thighs. Your rock solid cock is poking up against the smooth skin of her toned stomach.

“You want this punishment deep down, don't you?” you prod. She offers no response but you know to take that as a yes. She might just be the kinkiest singer around. She made a whole song about S&M for fucks sake. You bring the paddle down against her ass causing her already sore cheeks to start quaking once again. She lets out little whimpers and cries as the studs on the paddle further darken her already reddened flesh. Pretty soon the room is only full of the sounds of leather hitting skin and the sounds coming from Rihanna’s mouth. Her toned stomach and pussy rubbing up against you bare thighs has got you fully erect by now. You try to suppress groans as her writhing body rubs up against your member from all the abuse her ass is taking. You need some kind of relief at this point. You give her ten more strokes with the studded paddle before you roughly knead her ass in your large palm and pull her off your lap. You make her kneel in front of your rock hard cock as you grab the riding crop.

“Get that ass up and suck me baby.” you order more than ask. She nods and looks into your eyes as she starts stroking your hard shaft and licks a path up the underside to your tip. She wraps her lips around the sensitive glands and tongues the slit. You groan as you run your hand through her hair and strike her upturned ass with the riding crop. She groans against you cock and the vibrations feel amazing. That only serves as further motivation to strike her ass as hard as possible. You lash her ass with the crop, making it bounce and jiggle around as she takes your cock further into her mouth. She gently squeezes your balls and eagerly slurps the spurts of precum that she’s rewarded with. She takes your length deeper and deeper as your head is dragged across the ridges of the top of her mouth before hitting the softer flesh at the back of her throat.

“Fuck yeah baby girl. Take it all.” you order as you you lash her ass particularly hard causing her to squeal with your cock down her throat. She pushes further, taking almost your entire nine inches. She swallows around your hard dick, holding it in place a few seconds before bobbing her head up and down and swirling her tongue around the vein pulsing on the underside of your cock. You grab her hair and tilt her head slightly to get an unobstructed view of her pretty face as she deep throats you over and over. Her eyes are certainly something. This is too fucking hot. Your roughly lash her ass causing her to bob up and down faster, desperately sucking the length of your cock to get you to cum.

“Sh-Shit! Your too good at this you know that? Fuck I’m gonna cum!” you shout as you feel your balls tighten. When she pushes down to your base again and lets out a moan as you strike her ass again, you lose your control. You erupt into her throat as she swallows your hot cum and a few drops escape. She pulls her mouth off your semi-hard dick with a pop as she gazes lustily at you. You roughly grab her breasts and pinch her nipples as you pull her onto your lap and attack her neck with deep kisses. She groans as you suck on her pulse point and leave an angry red mark on her neck. You pinch and twist her nipples in your hands, causing her to cry out and whimper as you sensually bite her neck and shoulder. You let go off her breasts and wrap your lips around her rock hard nipples, roughly sucking on them and teasing them with your tongue. She moans in approval as you scrape your teeth across the hardened nub and you are rock hard once again.

“Fuck I need you. Get up here.” you order as she complies as she drags her wet folds across your hot length. You part her outer lips and gather some of her wetness before sticking your fingers into her mouth and making her own sweetness. You easily stick three fingers inside of her with your other hand as she cries out in pleasure. She’s so fucking wet. Your thighs are already glistened with her sweet juices.

“What do you want baby girl?” you ask as she just whimpers and moans at your fingers pumping inside of her.

“I-I need you daddy. Right now. I want your cock inside of me, filling me up. I-I took some birth control pills so I can have you raw.” she gets out. You let a smile show itself on your face. That’s a good girl. She positions herself in front of you, straddling your legs as you sit up properly, your cock standing hard. She lowered herself so your big cockhead entered her slick pussy and she kept on lowering herself until she took your entire length up her wanton pussy. She began to move slowly and you let her find her rhythm as she gets her feet planted on the floor and bounces on your dick. You love the feeling of your thick shaft piercing her, pushing against her clenching walls and filling her completely. 

“Fuck yeah babe, ride me like you mean it.” you moan as you thrust up every time she lowers herself, shoving your cock in as far as it will go. You wrap your arms around her as she leans back and brings her feet up so she can spread her legs and rest them on the bed. She looks amazing like this, pussy completely spread and riding your giant cock in earnest. You pump up into her as she rides you with a lewd squelching sound soon filling the room. You reach down and stroke her clit causing her to jolt on your cock and tumble into another orgasm. Her back arches and she tangles your hair in her hands as she presses down hard on your cock that’s still impaling her.

“Shit!” you cry. You aren’t too far behind her as you feel your cock swelling and spasming inside her clenching walls. Soon your shooting cum into Rihanna’s clenching core. You fill her up so much that some of the stuff begins to drip back out and a thick glob falls on the floor. Rihanna drops her feet back on the floor and rotates her hips on your still hard cock buried inside of her, forcing more cum to drip out of her pussy. Your hands never still pinching and pulling at her gorgeous, golden breasts. She slides off your lap and gets on her shaky legs.

“Damn daddy, your still hard? Maybe you need something else of mine?” she asks seductively as she stretches and spreads herself out on the bed.

“You just read my mind.” you respond with a grin as you go to grab some lube and lather your cock with the stuff. You then spread Rihanna’s ass and pour the lube directly over her anus before rubbing the cool substance in. Her previously tight little hole is already stretched out since you pumped it with your fingers pretty hard before. Nevertheless you shove a few fingers in and make sure she’s not too tight, causing her to moan as her ass clenches around your fingers. This is gonna feel great. You nudge your cock head against her hole and push in, moaning as the slick, constricting heat squeezes your member. You push in slowly, loving the view of your huge cock splitting her fat ass in half. You keep going until you bottom out, groin resting against juicy red buttocks. You ground in, deep and hard because you know the Barbadian wants to have her ass owned. She likes it when it hurts so good.

“Fu-Fuck! Yes daddy! Just like that! Ohhh you know me so well daddy!” she praises as you roughly grab her hips and pump her ass. You angle her so her swollen clit can mash against the soft fabric of the bedsheets. The pop star buries her head in the bed as she screams your name over and over, holding on for dear life as you roughly ream her ass. You slowly withdraw until your head is pressed against the inside of her anus and then roughly snap your hips forward, plunging your cock into the depths of her bowels. The image of your big cock sliding in and out of her little hole is fucking amazing as her ass cheeks clap together at the impact of it all. Rihanna wails as you slam into her again and she presses her sensitive core against the soft mattress.

“Ahh daddy...oh my....aghhh fuck!” she screams at the next grind of her battered clit against the mattress. She’s caught between so much ecstasy and agony right now that she just about can’t take anymore. Her cunt spasms around nothing and her ass clamps down hard around your cock. You hold her firmly in place as she falls apart beneath you, convulsing and shaking with the force of yet another climax. Your hands clutch at her curvy hips to push into the woman under you ass your cock pulses and twitches. You orgasm and paint her walls with thick semen as her ass keeps on clenching around your cock, milking every last drop out of you. You slowly pull out of her ass and slump right next to the heaving pop star. Both of you are completely spent.  
“Fuck baby, your too damn good.” you mutter as you both just lay there, completely exhausted.

“Yeah, that was perfect daddy.” she cooes as she slowly gets up and rubs her raw red, stretched out ass.

“Heh I really did a number on you huh?” you tease. She just smiles at you in her post orgasmic bliss and takes your hand. You get up and lead her out of the room to the bathroom. You two need a nice, warm shower. Surely you won’t get sidetracked right?

**Notes for the Chapter:**

> Sorry this took so long but I really like this one too. Hopefully it was worth the wait.


End file.
